Selected ATcT [1, 2] enthalpy of formation based on version 1.140 of the Thermochemical Network [3]

This version of ATcT results[3] was generated by additional expansion of version 1.130 to fully include the highest-level electronic structure computations described in reference [4].

2-Cyanovinyl

Formula: CHCHCN (g, anti)

CAS RN: 189141-20-6

ATcT ID: 189141-20-6*1

SMILES: [CH]=CC#N

InChI: InChI=1S/C3H2N/c1-2-3-4/h1-2H

InChIKey: ACZFFSJOJCAPKP-UHFFFAOYSA-N

Hills Formula: C3H2N1

2D Image:

Aliases: CHCHCN; 2-Cyanovinyl; 2-Cyanoethenyl

Relative Molecular Mass: 52.0547 ± 0.0024

Δ_fH°(0 K)	Δ_fH°(298.15 K)	Uncertainty	Units
448.18	445.72	± 0.97	kJ/mol

3D Image of CHCHCN (g, anti)

spin ON spin OFF

Top contributors to the provenance of Δ_fH° of CHCHCN (g, anti)

The 20 contributors listed below account only for 54.5% of the provenance of Δ_fH° of CHCHCN (g, anti).
A total of 94 contributors would be needed to account for 90% of the provenance.

Please note: The list is limited to 20 most important contributors or, if less, a number sufficient to account for 90% of the provenance. The Reference acts as a further link to the relevant references and notes for the measurement. The Measured Quantity is normaly given in the original units; in cases where we have reinterpreted the original measurement, the listed value may differ from that given by the authors. The quoted uncertainty is the a priori uncertainty used as input when constructing the initial Thermochemical Network, and corresponds either to the value proposed by the original authors or to our estimate; if an additional multiplier is given in parentheses immediately after the prior uncertainty, it corresponds to the factor by which the prior uncertainty needed to be multiplied during the ATcT analysis in order to make that particular measurement consistent with the prevailing knowledge contained in the Thermochemical Network.

Contribution (%)	TN ID	Reaction	Measured Quantity	Reference
7.4	7741.6	CHCHCN (g, syn) → CHCHCN (g, anti)	Δ_rH°(0 K) = 0.70 ± 1.0 kJ/mol	Johansen 2019, est unc
5.2	7739.1	3 CH4 (g) + NH3 (g) → CHCHCN (g, syn) + 13/2 H2 (g)	Δ_rH°(0 K) = 685.45 ± 3.0 kJ/mol	Klippenstein 2017
4.2	7749.5	CH2CHCN (g, singlet) + CH2CH (g) → CHCHCN (g, anti) + CH2CH2 (g)	Δ_rH°(0 K) = 2.99 ± 0.85 kcal/mol	Ruscic W1RO
3.8	7749.4	CH2CHCN (g, singlet) + CH2CH (g) → CHCHCN (g, anti) + CH2CH2 (g)	Δ_rH°(0 K) = 3.56 ± 0.90 kcal/mol	Ruscic CBS-n
3.8	7749.1	CH2CHCN (g, singlet) + CH2CH (g) → CHCHCN (g, anti) + CH2CH2 (g)	Δ_rH°(0 K) = 3.83 ± 0.90 kcal/mol	Ruscic G3X
3.8	7749.2	CH2CHCN (g, singlet) + CH2CH (g) → CHCHCN (g, anti) + CH2CH2 (g)	Δ_rH°(0 K) = 3.27 ± 0.90 kcal/mol	Ruscic G4
3.3	7743.1	CHCHCN (g, anti) → CH2CCN (g)	Δ_rH°(0 K) = -29.55 ± 4.0 kJ/mol	Johansen 2019, est unc
3.0	7749.3	CH2CHCN (g, singlet) + CH2CH (g) → CHCHCN (g, anti) + CH2CH2 (g)	Δ_rH°(0 K) = 2.62 ± 1.0 kcal/mol	Ruscic CBS-n
2.3	7742.1	CHCHCN (g, syn) → CH2CCN (g)	Δ_rH°(0 K) = -30.90 ± 3.0 kJ/mol	Klippenstein 2017
2.3	7729.5	CHCHCN (g, anti) → 3 C (g) + 2 H (g) + N (g)	Δ_rH°(0 K) = 618.79 ± 1.50 kcal/mol	Ruscic W1RO
2.0	7729.2	CHCHCN (g, anti) → 3 C (g) + 2 H (g) + N (g)	Δ_rH°(0 K) = 619.76 ± 1.60 kcal/mol	Ruscic G4
2.0	7729.4	CHCHCN (g, anti) → 3 C (g) + 2 H (g) + N (g)	Δ_rH°(0 K) = 617.30 ± 1.60 kcal/mol	Ruscic CBS-n
1.7	7729.1	CHCHCN (g, anti) → 3 C (g) + 2 H (g) + N (g)	Δ_rH°(0 K) = 619.48 ± 1.72 kcal/mol	Ruscic G3X
1.5	7731.5	CHCHCN (g, anti) → [CHCHCN]+ (g, anti triplet)	Δ_rH°(0 K) = 11.088 ± 0.040 eV	Ruscic W1RO
1.4	7748.5	CH2CHCN (g, singlet) → CHCHCN (g, anti) + H (g)	Δ_rH°(0 K) = 112.28 ± 1.50 kcal/mol	Ruscic W1RO
1.3	7742.2	CHCHCN (g, syn) → CH2CCN (g)	Δ_rH°(0 K) = -28.85 ± 4.0 kJ/mol	Johansen 2019, est unc
1.2	7748.2	CH2CHCN (g, singlet) → CHCHCN (g, anti) + H (g)	Δ_rH°(0 K) = 111.69 ± 1.60 kcal/mol	Ruscic G4
1.2	7748.4	CH2CHCN (g, singlet) → CHCHCN (g, anti) + H (g)	Δ_rH°(0 K) = 113.17 ± 1.60 kcal/mol	Ruscic CBS-n
1.1	7730.5	CHCHCN (g, syn) → 3 C (g) + 2 H (g) + N (g)	Δ_rH°(0 K) = 618.78 ± 1.50 kcal/mol	Ruscic W1RO
1.1	7729.3	CHCHCN (g, anti) → 3 C (g) + 2 H (g) + N (g)	Δ_rH°(0 K) = 617.83 ± 2.16 kcal/mol	Ruscic CBS-n

Top 10 species with enthalpies of formation correlated to the Δ_fH° of CHCHCN (g, anti)

Please note: The correlation coefficients are obtained by renormalizing the off-diagonal elements of the covariance matrix by the corresponding variances.
The correlation coefficient is a number from -1 to 1, with 1 representing perfectly correlated species, -1 representing perfectly anti-correlated species, and 0 representing perfectly uncorrelated species.

Correlation Coefficent (%)	Species Name	Formula	Δ_fH°(0 K)	Δ_fH°(298.15 K)	Uncertainty	Units	Relative Molecular Mass	ATcT ID
70.6	2-Cyanovinyl	CHCHCN (g, syn)	447.76	445.28	± 0.99	kJ/mol	52.0547 ± 0.0024	189141-20-6*2
70.6	2-Cyanovinyl	CHCHCN (g)	447.76	445.36	± 0.99	kJ/mol	52.0547 ± 0.0024	189141-20-6*0
32.7	Acrylonitrile	CH2CHCN (g, singlet)	193.81	187.05	± 0.66	kJ/mol	53.0627 ± 0.0024	107-13-1*1
32.7	Acrylonitrile	CH2CHCN (g)	193.81	187.05	± 0.66	kJ/mol	53.0627 ± 0.0024	107-13-1*0
32.2	2-Isocyanovinyl	CHCHNC (g)	543.2	541.8	± 1.7	kJ/mol	52.0547 ± 0.0024	225798-14-1*0
32.2	2-Isocyanovinyl	CHCHNC (g, anti)	543.2	541.2	± 1.7	kJ/mol	52.0547 ± 0.0024	225798-14-1*1
29.5	2-Isocyanovinyl	CHCHNC (g, syn)	544.6	542.6	± 1.7	kJ/mol	52.0547 ± 0.0024	225798-14-1*2
28.5	2-Cyanovinylium	[CHCHCN]+ (g, anti triplet)	1517.2	1515.1	± 1.8	kJ/mol	52.0542 ± 0.0024	85398-67-0*21
28.5	2-Cyanovinylium	[CHCHCN]+ (g, triplet)	1517.2	1515.2	± 1.8	kJ/mol	52.0542 ± 0.0024	85398-67-0*2
26.6	Acrylonitrile	CH2CHCN (cr,l)	146.32	153.98	± 0.77	kJ/mol	53.0627 ± 0.0024	107-13-1*500

Most Influential reactions involving CHCHCN (g, anti)

Please note: The list, which is based on a hat (projection) matrix analysis, is limited to no more than 20 largest influences.

Influence Coefficient	TN ID	Reaction	Measured Quantity	Reference
0.561	7741.6	CHCHCN (g, syn) → CHCHCN (g, anti)	Δ_rH°(0 K) = 0.70 ± 1.0 kJ/mol	Johansen 2019, est unc
0.198	7731.5	CHCHCN (g, anti) → [CHCHCN]+ (g, anti triplet)	Δ_rH°(0 K) = 11.088 ± 0.040 eV	Ruscic W1RO
0.135	7733.5	[CHCHCN]- (g, anti) → CHCHCN (g, anti)	Δ_rH°(0 K) = 1.871 ± 0.050 eV	Ruscic W1RO
0.105	7755.5	CHCHNC (g, anti) → CHCHCN (g, anti)	Δ_rH°(0 K) = -23.09 ± 1.2 kcal/mol	Ruscic W1RO
0.095	7743.1	CHCHCN (g, anti) → CH2CCN (g)	Δ_rH°(0 K) = -29.55 ± 4.0 kJ/mol	Johansen 2019, est unc
0.091	7733.2	[CHCHCN]- (g, anti) → CHCHCN (g, anti)	Δ_rH°(0 K) = 1.892 ± 0.061 eV	Ruscic G4
0.089	7755.4	CHCHNC (g, anti) → CHCHCN (g, anti)	Δ_rH°(0 K) = -22.20 ± 1.3 kcal/mol	Ruscic CBS-n
0.089	7755.2	CHCHNC (g, anti) → CHCHCN (g, anti)	Δ_rH°(0 K) = -22.52 ± 1.3 kcal/mol	Ruscic G4
0.077	7755.1	CHCHNC (g, anti) → CHCHCN (g, anti)	Δ_rH°(0 K) = -23.11 ± 1.4 kcal/mol	Ruscic G3X
0.077	7749.5	CH2CHCN (g, singlet) + CH2CH (g) → CHCHCN (g, anti) + CH2CH2 (g)	Δ_rH°(0 K) = 2.99 ± 0.85 kcal/mol	Ruscic W1RO
0.068	7749.4	CH2CHCN (g, singlet) + CH2CH (g) → CHCHCN (g, anti) + CH2CH2 (g)	Δ_rH°(0 K) = 3.56 ± 0.90 kcal/mol	Ruscic CBS-n
0.068	7749.1	CH2CHCN (g, singlet) + CH2CH (g) → CHCHCN (g, anti) + CH2CH2 (g)	Δ_rH°(0 K) = 3.83 ± 0.90 kcal/mol	Ruscic G3X
0.068	7749.2	CH2CHCN (g, singlet) + CH2CH (g) → CHCHCN (g, anti) + CH2CH2 (g)	Δ_rH°(0 K) = 3.27 ± 0.90 kcal/mol	Ruscic G4
0.059	7731.2	CHCHCN (g, anti) → [CHCHCN]+ (g, anti triplet)	Δ_rH°(0 K) = 11.115 ± 0.073 eV	Ruscic G4
0.059	7755.3	CHCHNC (g, anti) → CHCHCN (g, anti)	Δ_rH°(0 K) = -22.61 ± 1.6 kcal/mol	Ruscic CBS-n
0.056	7731.4	CHCHCN (g, anti) → [CHCHCN]+ (g, anti triplet)	Δ_rH°(0 K) = 11.034 ± 0.075 eV	Ruscic CBS-n
0.055	7749.3	CH2CHCN (g, singlet) + CH2CH (g) → CHCHCN (g, anti) + CH2CH2 (g)	Δ_rH°(0 K) = 2.62 ± 1.0 kcal/mol	Ruscic CBS-n
0.047	7733.1	[CHCHCN]- (g, anti) → CHCHCN (g, anti)	Δ_rH°(0 K) = 1.900 ± 0.085 eV	Ruscic G3X
0.043	7741.5	CHCHCN (g, syn) → CHCHCN (g, anti)	Δ_rH°(0 K) = -2 ± 300 cm-1	Ruscic W1RO
0.041	7733.4	[CHCHCN]- (g, anti) → CHCHCN (g, anti)	Δ_rH°(0 K) = 1.904 ± 0.090 eV	Ruscic CBS-n

References

1		B. Ruscic, R. E. Pinzon, M. L. Morton, G. von Laszewski, S. Bittner, S. G. Nijsure, K. A. Amin, M. Minkoff, and A. F. Wagner, Introduction to Active Thermochemical Tables: Several "Key" Enthalpies of Formation Revisited. J. Phys. Chem. A 108, 9979-9997 (2004) [DOI: 10.1021/jp047912y]
2		B. Ruscic, R. E. Pinzon, G. von Laszewski, D. Kodeboyina, A. Burcat, D. Leahy, D. Montoya, and A. F. Wagner, Active Thermochemical Tables: Thermochemistry for the 21^st Century. J. Phys. Conf. Ser. 16, 561-570 (2005) [DOI: 10.1088/1742-6596/16/1/078]
3		B. Ruscic and D. H. Bross, Active Thermochemical Tables (ATcT) values based on ver. 1.140 of the Thermochemical Network (2024); available at ATcT.anl.gov
4		J. H. Thorpe, J. L. Kilburn, D. Feller, P. B. Changala, D. H. Bross, B. Ruscic, and J. F. Stanton, Elaborated Thermochemical Treatment of HF, CO, N2, and H2O: Insight into HEAT and Its Extensions J. Chem. Phys. 155, 184109 (2021) [DOI: 10.1063/5.0069322]
5		B. Ruscic, Uncertainty Quantification in Thermochemistry, Benchmarking Electronic Structure Computations, and Active Thermochemical Tables. Int. J. Quantum Chem. 114, 1097-1101 (2014) [DOI: 10.1002/qua.24605]
6		B. Ruscic and D. H. Bross, Thermochemistry Computer Aided Chem. Eng. 45, 3-114 (2019) [DOI: 10.1016/B978-0-444-64087-1.00001-2]

Formula

The aggregate state is given in parentheses following the formula, such as: g - gas-phase, cr - crystal, l - liquid, etc.

Uncertainties

The listed uncertainties correspond to estimated 95% confidence limits, as customary in thermochemistry (see, for example, Ruscic [5] and Ruscic and Bross[6]).
Note that an uncertainty of ± 0.000 kJ/mol indicates that the estimated uncertainty is < ± 0.000₅ kJ/mol.

Website Functionality Credits

The reorganization of the website was developed and implemented by David H. Bross (ANL).
The find function is based on the complete Species Dictionary entries for the appropriate version of the ATcT TN.
The molecule images are rendered by Indigo-depict.
The XYZ renderings are based on Jmol: an open-source Java viewer for chemical structures in 3D. http://www.jmol.org/.

Acknowledgement

This work was supported by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences, Division of Chemical Sciences, Geosciences and Biosciences under Contract No. DE-AC02-06CH11357.